CA1104151A - Hydrazinium phosphites (fungicides) - Google Patents
Hydrazinium phosphites (fungicides)Info
- Publication number
- CA1104151A CA1104151A CA296,719A CA296719A CA1104151A CA 1104151 A CA1104151 A CA 1104151A CA 296719 A CA296719 A CA 296719A CA 1104151 A CA1104151 A CA 1104151A
- Authority
- CA
- Canada
- Prior art keywords
- phosphite
- hydrazinium
- general formula
- radicals
- branched
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LDGDZTJIEKLCTK-UHFFFAOYSA-N NN.NN.NN.OP(O)O Chemical class NN.NN.NN.OP(O)O LDGDZTJIEKLCTK-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000000417 fungicide Substances 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- -1 nitro-substituted phenyl Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 235000007164 Oryza sativa Nutrition 0.000 claims description 7
- 235000009566 rice Nutrition 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 6
- 208000031888 Mycoses Diseases 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ASGGODFMKDMRFF-UHFFFAOYSA-N CCOP(O)O.NN.NN Chemical compound CCOP(O)O.NN.NN ASGGODFMKDMRFF-UHFFFAOYSA-N 0.000 claims description 2
- 241000209094 Oryza Species 0.000 claims 2
- VDOROYQZMLNEAB-UHFFFAOYSA-N CCOP(O)O.NNC1=CC=CC=C1.NNC1=CC=CC=C1 Chemical compound CCOP(O)O.NNC1=CC=CC=C1.NNC1=CC=CC=C1 VDOROYQZMLNEAB-UHFFFAOYSA-N 0.000 claims 1
- BHJUZKKYKQOGON-UHFFFAOYSA-N COP(O)O.NNC1=CC=CC=C1.NNC1=CC=CC=C1 Chemical compound COP(O)O.NNC1=CC=CC=C1.NNC1=CC=CC=C1 BHJUZKKYKQOGON-UHFFFAOYSA-N 0.000 claims 1
- RUVILQADKRQZNL-UHFFFAOYSA-N NNC(C=C1)=CC=C1[N+]([O-])=O.NNC(C=C1)=CC=C1[N+]([O-])=O.NNC(C=C1)=CC=C1[N+]([O-])=O.OP(O)O Chemical compound NNC(C=C1)=CC=C1[N+]([O-])=O.NNC(C=C1)=CC=C1[N+]([O-])=O.NNC(C=C1)=CC=C1[N+]([O-])=O.OP(O)O RUVILQADKRQZNL-UHFFFAOYSA-N 0.000 claims 1
- VKARRLDMFMRVAD-UHFFFAOYSA-N NNC1=CC=CC=C1.NNC1=CC=CC=C1.NNC1=CC=CC=C1.OP(O)O Chemical compound NNC1=CC=CC=C1.NNC1=CC=CC=C1.NNC1=CC=CC=C1.OP(O)O VKARRLDMFMRVAD-UHFFFAOYSA-N 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 7
- 239000011149 active material Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 231100000674 Phytotoxicity Toxicity 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 241000233866 Fungi Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000222199 Colletotrichum Species 0.000 description 2
- 235000009075 Cucumis anguria Nutrition 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000047703 Nonion Species 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- PMKSYFHQMOKKAG-UHFFFAOYSA-N [NH3+]N.[NH3+]N.[O-]P([O-])=O Chemical class [NH3+]N.[NH3+]N.[O-]P([O-])=O PMKSYFHQMOKKAG-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7704981A FR2380286A1 (fr) | 1977-02-14 | 1977-02-14 | Nouveaux derives de phosphites d'hydrazinium |
| FR77/04981 | 1977-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1104151A true CA1104151A (en) | 1981-06-30 |
Family
ID=9187017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA296,719A Expired CA1104151A (en) | 1977-02-14 | 1978-02-10 | Hydrazinium phosphites (fungicides) |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4188381A (fi) |
| JP (1) | JPS53103421A (fi) |
| AR (1) | AR219936A1 (fi) |
| AU (1) | AU518709B2 (fi) |
| BE (1) | BE863945A (fi) |
| BG (2) | BG28558A3 (fi) |
| BR (1) | BR7800880A (fi) |
| CA (1) | CA1104151A (fi) |
| CH (1) | CH628904A5 (fi) |
| CS (1) | CS196416B2 (fi) |
| DD (1) | DD135558A5 (fi) |
| DE (1) | DE2805941C2 (fi) |
| DK (1) | DK63978A (fi) |
| ES (1) | ES466912A1 (fi) |
| FR (1) | FR2380286A1 (fi) |
| GB (1) | GB1566670A (fi) |
| GR (1) | GR64460B (fi) |
| HU (1) | HU178689B (fi) |
| IE (1) | IE46664B1 (fi) |
| IL (1) | IL54033A0 (fi) |
| IT (1) | IT1155823B (fi) |
| LU (1) | LU79059A1 (fi) |
| NL (1) | NL188160C (fi) |
| OA (1) | OA05888A (fi) |
| PH (1) | PH13855A (fi) |
| PL (1) | PL107650B1 (fi) |
| PT (1) | PT67647B (fi) |
| SU (1) | SU708982A3 (fi) |
| TR (1) | TR19907A (fi) |
| YU (1) | YU33978A (fi) |
| ZA (1) | ZA78830B (fi) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2419675A1 (fr) * | 1978-03-16 | 1979-10-12 | Philagro Sa | Compositions fongicides a base de phosphites d'isothiouronium |
| HU184319B (en) * | 1980-08-27 | 1984-08-28 | Borsodi Vegyi Komb | Fungicide compositions salts of phosphonoic acid-monoesters and process for producing the active agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773796A (en) * | 1952-09-26 | 1956-12-11 | Shell Dev | Method of protecting plants from fungi by applying hydrazine salts of inorganic phosphorous acids |
| US2850425A (en) * | 1954-09-21 | 1958-09-02 | Monsanto Chemicals | Fungicidal composition comprising an aromatic hydrazine |
| TR19072A (tr) * | 1973-11-26 | 1978-05-01 | Pepro | Fosforlu tuerevler ihtiva eden fungisid terkipler |
| DE2463046C2 (de) | 1973-12-14 | 1984-05-03 | PEPRO - Société pour le Développement et la Vente de Spécialités Chimiques, Lyon | Fungizide Mittel auf Ammoniumphosphonatbasis |
-
1977
- 1977-02-14 FR FR7704981A patent/FR2380286A1/fr active Granted
-
1978
- 1978-01-13 BG BG038392A patent/BG28558A3/xx unknown
- 1978-01-26 US US05/872,435 patent/US4188381A/en not_active Expired - Lifetime
- 1978-01-31 PH PH20733A patent/PH13855A/en unknown
- 1978-02-07 TR TR19907A patent/TR19907A/xx unknown
- 1978-02-08 NL NLAANVRAGE7801432,A patent/NL188160C/xx not_active IP Right Cessation
- 1978-02-10 GB GB5540/78A patent/GB1566670A/en not_active Expired
- 1978-02-10 IE IE295/78A patent/IE46664B1/en not_active IP Right Cessation
- 1978-02-10 CA CA296,719A patent/CA1104151A/en not_active Expired
- 1978-02-10 ZA ZA00780830A patent/ZA78830B/xx unknown
- 1978-02-10 AU AU33204/78A patent/AU518709B2/en not_active Expired
- 1978-02-13 OA OA56409A patent/OA05888A/xx unknown
- 1978-02-13 PL PL1978204591A patent/PL107650B1/pl unknown
- 1978-02-13 JP JP1527578A patent/JPS53103421A/ja active Granted
- 1978-02-13 IT IT48026/78A patent/IT1155823B/it active
- 1978-02-13 IL IL54033A patent/IL54033A0/xx not_active IP Right Cessation
- 1978-02-13 GR GR55444A patent/GR64460B/el unknown
- 1978-02-13 DE DE2805941A patent/DE2805941C2/de not_active Expired
- 1978-02-13 AR AR271081A patent/AR219936A1/es active
- 1978-02-13 DD DD78203680A patent/DD135558A5/xx unknown
- 1978-02-13 ES ES466912A patent/ES466912A1/es not_active Expired
- 1978-02-13 HU HU78PI612A patent/HU178689B/hu unknown
- 1978-02-13 SU SU782577851A patent/SU708982A3/ru active
- 1978-02-13 LU LU79059A patent/LU79059A1/xx unknown
- 1978-02-13 DK DK63978A patent/DK63978A/da unknown
- 1978-02-13 PT PT67647A patent/PT67647B/pt unknown
- 1978-02-13 BG BG038665A patent/BG28559A3/xx unknown
- 1978-02-14 CS CS78958A patent/CS196416B2/cs unknown
- 1978-02-14 BE BE185156A patent/BE863945A/xx not_active IP Right Cessation
- 1978-02-14 CH CH161478A patent/CH628904A5/fr not_active IP Right Cessation
- 1978-02-14 YU YU00339/78A patent/YU33978A/xx unknown
- 1978-02-14 BR BR7800880A patent/BR7800880A/pt unknown
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